反应详情

温度

-78 °C

LiHMDS (1.0M in THF, 16.8 mL, 16.8 mmol) was added dropwise to a stirred solution of aniline (821 mg, 8.80 mmol) in anhydrous THF (20 mL) under a nitrogen atmosphere at −78° C. After 10 min stirring at −78° C., a solution of 2-bromo-1,3-difluoro-4-nitrobenzene (2.0 g, 8.40 mmol) in THF (10 mL) was added and stirring at −78° C. was continued for 30 min. The reaction mixture was quenched by addition of water and extracted with EtOAc (×3). The combined organic fractions were washed with brine, dried (MgSO4), concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane) to afford the title compound (2.4 g, 91%). 1H NMR (CDCl3, 400 MHz): δ 8.48 (1H, s), 8.19-7.12 (1H, m), 7.33-7.25 (2H, m), 7.09 (1H, t, J=7.41 Hz), 6.93-6.83 (3H, m).

1. stirringstirring at −78° C.
2. waitwas continued for 30 min
3. customThe reaction mixture was quenched by addition of water
4. extractionextracted with EtOAc (×3)
5. washThe combined organic fractions were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane)